sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate

• ChemBase ID: 133937
• Molecular Formular: C15H13NaO9
• Molecular Mass: 360.24809
• Monoisotopic Mass: 360.04572628
• SMILES: c1cc(cc2c1ccc(=O)o2)O[C@H]1[C@@H]([C@H]([C@@H]([C@H](O1)C(=O)[O-])O)O)O.[Na+]
• Canonical SMILES: [O-]C(=O)[C@H]1O[C@@H](Oc2ccc3c(c2)oc(=O)cc3)[C@@H]([C@H]([C@@H]1O)O)O.[Na+]
• InChI: InChI=1S/C15H14O9.Na/c16-9-4-2-6-1-3-7(5-8(6)23-9)22-15-12(19)10(17)11(18)13(24-15)14(20)21;/h1-5,10-13,15,17-19H,(H,20,21);/q;+1/p-1/t10-,11-,12+,13-,15+;/m0./s1
• InChIKey: SKHLGBDGEPDEME-KSOKONAESA-M

NAMES AND DATABASE IDS

Names

• IUPAC name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-oxo-2H-chromen-7-yl)oxy]oxane-2-carboxylate
• IUPAC Traditional name: sodium (2S,3S,4S,5R,6S)-3,4,5-trihydroxy-6-[(2-oxochromen-7-yl)oxy]oxane-2-carboxylate
• Synonyms: 2-Oxo-2H-1-benzopyran-7-yl β-D-Glucopyranosiduronic Acid Monosodium Salt; Umbelliferyl β-D-Glucuronide Sodium Salt; 7-Hydroxy Coumarin β-D-Glucuronide Sodium Salt; Umbelliferyl β-D-glucuronide; 7-Hydroxycoumarin β-D-glucuronide sodium salt; 7-Hydroxy-2H-1-benzopyran-2-one glucuronide sodium salt; Umbelliferone glucuronide sodium salt; 7-Hydroxycoumarin glucuronide sodium salt

Database IDs

• CAS Number: 168286-98-4; 66695-14-5(freeacid)
• MDL Number: MFCD00674902
• PubChem SID: 24724651; 162228214
• PubChem CID: 23675380

CALCULATED PROPERTIES

• Acid pKa: 2.979382
• H Acceptors: 8
• H Donor: 3
• LogD (pH = 5.5): -2.9493296
• LogD (pH = 7.4): -3.9449944
• Log P: -0.46799925
• Molar Refractivity: 86.3784 cm^3
• Polarizability: 29.936827 Å^3
• Polar Surface Area: 145.58 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Water
• Apperance: Off-White Solid; white to faint yellow
• Melting Point: >200°C (dedf.); ≥285 °C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 20/21/22
• Safety Statements: 36
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302-H312-H332
• GHS Precautionary statements: P280
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves; Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥95%
• Empirical Formula (Hill Notation): C15H13NaO9

DETAILS

Sigma Aldrich - H6029

Biochem/physiol Actions
Metabolite of 7-ethoxycoumarin and coumarin. Useful as a pharmacokinetic standard in in vitro metabolic studies.

Sigma Aldrich - UC263

Application
Phase II (UDP-GT) metabolite of 7-hydroxycoumarin.

Toronto Research Chemicals - H924880

A metabolite of 7-Ethoxycoumarin and Coumarin. Useful as a pharmacokinetic standard in metabolic studies.

REFERENCES

• Blankson, E., et al.: Biochem. Pharmacol., 42, 1241 (1991)
• Steensma, A., et al.: Xenobiotica, 24, 893 (1991)
• Fisher, R., et al.: Toxicol. Methods, 5, 99 (1991)
• Ekins, S., et al.: Drug Metab. Dispos., 24, 990 (1996)